Carbon Tetrachloride → 1-(Chloromethyl)-4-phenoxybenzene

HRID 1693827Notes

Reaction equation

[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:36]>>[Cl:36][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

Reactant 3

HCID 5943Carbon Tetrachloride

HCID 11776Triphenylphosphine

HCID 826195(4-Phenoxyphenyl)methanol

Product 1

HCID 5209941-(Chloromethyl)-4-phenoxybenzeneYield 92%

Procedure

To a solution of (4-phenoxy-phenyl)-methanol (408 mg, 2.04 mmol) in carbon tetrachloride (8.2 mL) was added triphenylphosphine (642 mg, 2.45 mmol) under nitrogen atmosphere at room temperature, and the reaction solution was stirred under reflux for 7 hours and 40 minutes. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (409 mg, 92%).

Workup

temperatureunder reflux for 7 hours and 40 minutes
concentrationconcentrated under a reduced pressure
customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-f480deef976045388fd99ed63fc0ab3b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158657B2

Reaction notes

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